8-bromo-3-cyclopropylcarbonyl-5-methyl-1-indolizinecarbonitrile | 1217864-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 8-bromo-3-cyclopropylcarbonyl-5-methyl-1-indolizinecarbonitrile
• 英文别名: 8-bromo-3-(cyclopropanecarbonyl)-5-methylindolizine-1-carbonitrile
• CAS: 1217864-10-2
• 化学式: C₁₄H₁₁BrN₂O
• 分子量: 303.158
• InChiKey: NFZYOSOZVKIONF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(5-Bromo-2-methylpyridin-1-ium-1-yl)-1-cyclopropylethanone;bromide 、 丙烯腈 在 tetrakispyridinecobalt(II) di(chromate) 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以75%的产率得到8-bromo-3-cyclopropylcarbonyl-5-methyl-1-indolizinecarbonitrile
  参考文献：
  名称：

  Synthesis and antiproliferative activity of indolizine derivatives incorporating a cyclopropylcarbonyl group against Hep-G2 cancer cell line

  摘要：

  Indolizine and annulated indolizine derivatives incorporating a cyclopropylcarbonyl group were synthesized in a one pot procedure by the tanden reactions of [3 + 2] cycloaddition of the corresponding N-ylide with electron deficient alkene. Seventeen indolizine derivatives were reported for the first time. All the compounds were examined for their antiproliferative activity against the human hepatocellular liver carcinoma (Hep-G2) cell line by MTT method. Among the compounds tested, 5a, 5d, 5g and 5j showed the most favorable activities with IC50 values of 0.39, 0.48, 0.29 and 0.20 mu g/mL. Especially, compound 5j displayed potent antiproliferative activities with IC50 value of 0.20 mu g/mL, and showed significant EGFR kinase inhibitory activity with IC50 value of 0.085 mu M. Docking simulations of 5j were carried out to illustrate the binding mode of the molecular into the EGFR active site. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.02.056

文献信息

• Synthesis and antiproliferative activity of indolizine derivatives incorporating a cyclopropylcarbonyl group against Hep-G2 cancer cell line
  作者：Yong-Miao Shen、Peng-Cheng Lv、Wu Chen、Peng-Gang Liu、Ming-Zhu Zhang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2010.02.056

  日期：2010.7

  Indolizine and annulated indolizine derivatives incorporating a cyclopropylcarbonyl group were synthesized in a one pot procedure by the tanden reactions of [3 + 2] cycloaddition of the corresponding N-ylide with electron deficient alkene. Seventeen indolizine derivatives were reported for the first time. All the compounds were examined for their antiproliferative activity against the human hepatocellular liver carcinoma (Hep-G2) cell line by MTT method. Among the compounds tested, 5a, 5d, 5g and 5j showed the most favorable activities with IC50 values of 0.39, 0.48, 0.29 and 0.20 mu g/mL. Especially, compound 5j displayed potent antiproliferative activities with IC50 value of 0.20 mu g/mL, and showed significant EGFR kinase inhibitory activity with IC50 value of 0.085 mu M. Docking simulations of 5j were carried out to illustrate the binding mode of the molecular into the EGFR active site. (C) 2010 Elsevier Masson SAS. All rights reserved.